Sodium Hydroxide → HCID 555082, compound

Participants

Reaction Steps

From 6-methoxy-4-methyl-8-phthalimido-5-(3-trifluoromethylphenoxy)quinoline-1-oxide Ethanolate (III): A solution of 6-methoxy-4-methyl-8-phthalimido-5-(3-trifluoromethylphenoxy)quinoline-1-oxide ethanolate (32.7g, 60.5 mmol) in CHCl3 (500 mL) was treated with POCl3 (55 mL, 92 g, 602 mmol) over 15 min. The solution was refluxed 2 hours, cooled, poured onto ice (1500 mL) and the pH was adjusted to 12 with 20% NaOH (700 g). The separated aqueous layer was extracted with CHCl3 (2×200 mL). The extract was washed with H2O (2×200 mL), saturated NaHCO3 (20 mL), dried (MgSO4) and evaporated in vacuo to a white solid. Recrystallization from ethanol gave 23.2 g (75%) of 1st crop title compound, mp 227°-229° C. Further recrystallizations did not change the melting point.

Provenance & Evidence